Abstract
It is shown that the 1,3-diaryldihydrobenzo[f]quinazolines that are formed in the condensation of β-naphthylamine, an aromatic aldehyde, and ammonia are 1,2-dihydro isomers. They readily form salts due to the developing stabilization of the molecule by resonance of the amidinium type. Thus 2,4-dialkylbenzo [f] quinazolinium iodides rather than monoalkyl derivatives were obtained in the case of alkylation with alkyl halides as a result of refluxing the reaction mixtures. The isomeric monoalkylbenzoquinazolinium iodides, the structure of which was proved by the formation of the known benzoquinazolines after treatment with alkali, were also obtained.
Similar content being viewed by others
Literature cited
V. P. Borovik, L. Yu. Ivanovskaya, and V. P. Mamaev, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim., Nauk, No. 14, 110 (1977).
M. A. Mikhaleva, G. N. Chernikova, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 1, 100 (1978).
A. Weissberger (editor), The Chemistry of Heterocyclic Compounds, Vol. 24, Part I, Wiley-Interscience (1967).
R. F. Smith, P. C. Briggs, R. A. Kent, J. A. Albricht, and E. J. Walsh, J. Heterocycl. Chem., 2, 157 (1965).
J. G. Smith, J. M. Sheepy, and E. M. Levy, J. Org. Chem., 41, 497 (1976).
J. G. Smith, and J. M. Sheepy, J. Heterocycl. Chem., 12, 231 (1975).
M. Lora-Tamayo, R. Madronero, and G. G. Munoz, Chem. Ber., 94, 208 (1961).
G. Kempter, H.-J. Ziegner, and G. Moser, Z. Chem., 11, 12 (1971).
R. B. Williams, J. Am. Chem. Soc., 64, 1395 (1942).
W. L. F. Armarego, J. Chem. Soc., No. 7, 2697 (1961).
K. Yamauchi, M. Hayashi, and M. Kinoshita, J. Org. Chem., 40, 385 (1975).
O. A. Zagulyaeva, and V. P. Mamaev, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 12, 137 (1968).
R. V. Coombs, R. P. Danna, M. Denzer, G. E. Hardtmann, B. Huegi, G. Koletar, and H. Ott, J. Med. Chem., 16, 1237 (1973).
N. V. Sidgwick, The Organic Chemistry of Nitrogen, Clarendon Press, Oxford (1966), pp. 421, 438.
Y. Yamada, T. Oine, and I. Inoue, Bull. Chem. Soc. Jpn., 47, 343 (1974).
D. Lloyd and H. J. McNab, J. Chem. Soc., Perkin Trans. I, No. 16, 1784 (1976).
N. J. Leonard and L. E. Brady, J. Org. Chem., 30, 817 (1965).
T. L. Pilicheva, O. N. Chupakhin, and I. Ya. Postovskii, Khim. Geterotsikl. Soedin., No. 4, 561 (1975).
W. Girke, Tetrahedron Lett., No. 39, 3537 (1976).
D. Lloyd and H. McNab, Angew. Chem., 88, 496 (1976).
Author information
Authors and Affiliations
Additional information
See [1] for communication LXIII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1259–1264, September, 1978.
Rights and permissions
About this article
Cite this article
Mikhaleva, M.A., Chernikova, G.N. & Mamaev, V.P. Pyrimidines. Chem Heterocycl Compd 14, 1019–1024 (1978). https://doi.org/10.1007/BF00509564
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00509564